US4829092A - Glycerol and diglycerol mixtures for skin moisturizing - Google Patents

Glycerol and diglycerol mixtures for skin moisturizing Download PDF

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Publication number
US4829092A
US4829092A US07/078,425 US7842587A US4829092A US 4829092 A US4829092 A US 4829092A US 7842587 A US7842587 A US 7842587A US 4829092 A US4829092 A US 4829092A
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US
United States
Prior art keywords
glycerol
skin
diglycerol
minutes
humectant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US07/078,425
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English (en)
Inventor
Bruce J. Nelson
Joseph D. Melnik
William H. Schmitt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chesebrough Ponds Inc
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Chesebrough Ponds Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Chesebrough Ponds Inc filed Critical Chesebrough Ponds Inc
Priority to US07/078,425 priority Critical patent/US4829092A/en
Assigned to CHESEBROUGH-POND'S INC., WESTPORT, CONNECTICUT A CORP. OF NEW YORK reassignment CHESEBROUGH-POND'S INC., WESTPORT, CONNECTICUT A CORP. OF NEW YORK ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: MELNIK, JOSEPH D., NELSON, BRUCE J., SCHMITT, WILLIAM H.
Priority to CA000572713A priority patent/CA1325599C/en
Priority to AU19748/88A priority patent/AU610911B2/en
Priority to DE8888306801T priority patent/DE3871640T2/de
Priority to EP19880306801 priority patent/EP0301781B1/en
Priority to ES198888306801T priority patent/ES2033434T3/es
Priority to AT88306801T priority patent/ATE76744T1/de
Priority to PH37288A priority patent/PH25093A/en
Priority to BR8803709A priority patent/BR8803709A/pt
Priority to IN206/BOM/88A priority patent/IN166787B/en
Priority to JP63187967A priority patent/JPH07106967B2/ja
Priority to ZA885491A priority patent/ZA885491B/xx
Publication of US4829092A publication Critical patent/US4829092A/en
Application granted granted Critical
Priority to GR920401934T priority patent/GR3005608T3/el
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures

Definitions

  • the present invention relates to novel skin conditioning compositions which are retentive on skin thereby reducing moisture loss from the skin surface.
  • Continuous or prolonged immersion in soap or detergent can contribute to dryness of the stratum corneum in that the surfactant medium promotes dissolution of the stratum corneum lipids or epidermal lipids, and the hydroscoic water-soluble components in the corneum.
  • emollient creams To alleviate skin dryness, emollient creams have been recommended for application to the skin.
  • the active ingredients in emollient creams probably increase the state of hydration of the corneous layer of the skin by altering the rate of diffusion of water from the skin layers, the rate of evaporation of water from the stratum corneum lipids or epidermal lipids and the ability of the corneous layer to hold moisture.
  • a wide variety of materials have been disclosed for alleviating the problems of dry skin.
  • a number of polyalcohols or derivatives such as glycerol and glycerol ethers have been used.
  • Glycerol is frequently used because of its excellent humectant properties.
  • Glycerol ethers such as the monoalkyl ethers have found wide spread commercial utility as base materials for cosmetic compositions.
  • diglycerol can be used as a moistening agent in cosmetic preparations (Japanese Kokai No. 74 41 545-Chem. Abstr., 81 1974 96335j and Japanese Kokai No. 73 91 231-Chem. Abstr., 80 1974 124594t).
  • An emollient cream is disclosed containing beeswax, stearic acid, polawax, various oils, isopropyl myristate, preservatives, and perfumes.
  • the synergistic effect of the blend is unexpected since the polyethers of glycerol are, in general, less effective humectants than glycerol itself, particularly as the number of repeating glycerol groups in the polyether increases.
  • FIG. 1 is a graph showing the effectiveness of the composition of the invention based on the data of Example 1.
  • Diglycerol is generally considered a diether of glycerol.
  • the material is generally a clear, odorless, colorless viscous liquid having a boiling point of approximately 205° C. at 1 mm Hg pressure.
  • the produce has a molecular weight of approximately 166, has four pendant hydroxy groups, and has a viscosity of about 280 centistokes at 65° C.
  • the diglycerol can be used in a weight ratio to glycerol ranging from 90:10 to about 10:90, preferably from about 75:25 to about 25:75 with preferred results being obtained at weight ratios of from about 40:60 to about 60:40.
  • This combination can be used in an amount sufficient to provide a humectant effect in a final use product.
  • the synergistic admixture can be used as a direct replacement for humectants in present formulations in like amounts.
  • the combination is used in an amount ranging from about 1% to about 30%, based on the total weight of the ingredients (including water) in the final composition.
  • humectants of the present invention can be used in any composition which presently uses humectants, primarily cosmetics, though the compositions of the invention can be used in other areas, such as pharmaceutical creams and lotions for topical application and in food products.
  • compositions of the invention can be used in such products as antiperspirants; bath and shower soaps, granules, bars, oils or gels; after-bath creams and lotions; shampoo and conditioners; makeup including base or foundation, blush, rouge, eye liner, eye shadow, mascara, and lip gloss; lip moisturizers and lip ointment; message creams and lotions; sun screen, sun tanning and skin bleaching compositions; skin paint; wrinkle remover; cold creams, cleansing creams, emollient creams and hand creams; perfume and fragrances; hair waving, bleaching, setting products, rinses and dressings; insect repellents, preshave and after-shave lotions and creams, shave creams, depilatories and the like.
  • the products can be in the form of creams, lotions, liquids, powders, pastes, and the like, as would be appreciated by one of ordinary skill in the art.
  • the final product such as a cosmetic lotion or cream
  • the final product can contain any of those various ingredients normally included within compositions of those types.
  • compositions may also contain agents suitable for aesthetic purposes such as perfumes and dyes. These agents may be used in amounts sufficient to achieve the desired fragrance and color.
  • the pH of the present compositions is preferably in the range of about 4.5-9.0.
  • compositions of the present invention generally have a cream or lotion consistency and may be in the form of oil-in-water or water-in-oil emulsions with the former being preferred because of their more pleasing cosmetic properties.
  • Methods of manufacturing the products are well known ("Cosmetics; Science & Technology", Ibid) and can be used in preparing compositions including the humectant composition of the present invention.
  • compositions of the present invention are useful in the skin care field generally. They are used in an amount sufficient to meet the individual user's needs and desires.
  • glycerol and diglycerol as an efficacious moisturizer was examined used an in vitro porcine skin assay. 4 ⁇ 1 centimeter pieces of hairless porcine skin were rinsed to remove irradiation residue, dried for more than 48 hours at 0% relative humidity and weighed. Pieces of skin were hydrated for 5 minutes in aqueous test solutions containing 10% (V/V) of the material being tested. The skin samples were then patted dry.
  • the skin samples were dehydrated for 24 hours in a desiccator at 0% relative humidity and weighed (Product Residue-%).
  • the samples were rehydrated for 24 hours at 100% relative humidity. The samples were allowed to dry while on an electric balance in an atmosphere of less than 10% relative humidity. Sample weights were taken at 0 minutes (moisture pickup-%) and after 10, 20, 30 and 60 minutes (Moisture Retention 10, 20, 30 and 60-%). The samples were then rinsed for 5 minutes in deionized water, dried for 24 hours and weighed to determine skin adherence or substantivity under wash conditions (Substantivity-%).
  • the combination of 5% glycerol/5% diglycerol provides an increased moisture pickup and moisture retention greater than that provided by 10% of either agent alone, and significantly greater than those results expected from the additive total of the two at the same concentration level (5%).
  • the moisture retention provided by the 5%:5% blend of glycerol/diglycerol after 60 minutes is substantially equivalent to that provided by diglycerol at the 10% level, 6.15% vs. 7.92%.
  • the moisture retention after 60 minutes for glycerol has been reduced to less than 1.
  • the moisture retention after 60 minutes is 1/14 that of the blend and at 5% glycerol the moisture retention after 60 minutes is 1/6 that of the blend.
  • a commercial hand care lotion was formulated using a blend of 2.5 parts glycerol/2.5 parts diglycerol in place of the 5 parts glycerol normally used in the lotions, the following formulation was used:
  • the lotion also contained methyl and propyl paraben as well as disodium EDTA as preservatives, color and fragrance.
  • the product of Sample F showed a significantly greater percent residue over that of the commercial lotion (G). Maximum moisture uptake was substantially equivalent between the product of the invention (F) and the commercial product (G). At moisture retentions of 10 and 20 minutes, the dry out between the two samples was essentially the same. At 30 minutes the moisture retention curves begin to deviate. After 60 minutes the products are significantly different.
  • the percent substantivity of the commercial product is significantly greater than the product of the invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Plant Substances (AREA)
US07/078,425 1987-07-27 1987-07-27 Glycerol and diglycerol mixtures for skin moisturizing Expired - Lifetime US4829092A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US07/078,425 US4829092A (en) 1987-07-27 1987-07-27 Glycerol and diglycerol mixtures for skin moisturizing
CA000572713A CA1325599C (en) 1987-07-27 1988-07-21 Cosmetic composition
AU19748/88A AU610911B2 (en) 1987-07-27 1988-07-22 Glycerol and diglycerol mixtures for skin moisturising
DE8888306801T DE3871640T2 (de) 1987-07-27 1988-07-25 Kosmetische zusammensetzung.
EP19880306801 EP0301781B1 (en) 1987-07-27 1988-07-25 Cosmetic composition
ES198888306801T ES2033434T3 (es) 1987-07-27 1988-07-25 Composicion cosmetica.
AT88306801T ATE76744T1 (de) 1987-07-27 1988-07-25 Kosmetische zusammensetzung.
IN206/BOM/88A IN166787B (enrdf_load_stackoverflow) 1987-07-27 1988-07-26
PH37288A PH25093A (en) 1987-07-27 1988-07-26 Glycerol and diglycerol mixtures for skin moisturising
BR8803709A BR8803709A (pt) 1987-07-27 1988-07-26 Umectante para uma composicao de tratamento de pele e a respectiva composicao
JP63187967A JPH07106967B2 (ja) 1987-07-27 1988-07-27 皮膚湿潤用グリセロール及びジグリセロール混合物
ZA885491A ZA885491B (en) 1987-07-27 1988-07-27 Cosmetic composition
GR920401934T GR3005608T3 (enrdf_load_stackoverflow) 1987-07-27 1992-09-03

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/078,425 US4829092A (en) 1987-07-27 1987-07-27 Glycerol and diglycerol mixtures for skin moisturizing

Publications (1)

Publication Number Publication Date
US4829092A true US4829092A (en) 1989-05-09

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US07/078,425 Expired - Lifetime US4829092A (en) 1987-07-27 1987-07-27 Glycerol and diglycerol mixtures for skin moisturizing

Country Status (13)

Country Link
US (1) US4829092A (enrdf_load_stackoverflow)
EP (1) EP0301781B1 (enrdf_load_stackoverflow)
JP (1) JPH07106967B2 (enrdf_load_stackoverflow)
AT (1) ATE76744T1 (enrdf_load_stackoverflow)
AU (1) AU610911B2 (enrdf_load_stackoverflow)
BR (1) BR8803709A (enrdf_load_stackoverflow)
CA (1) CA1325599C (enrdf_load_stackoverflow)
DE (1) DE3871640T2 (enrdf_load_stackoverflow)
ES (1) ES2033434T3 (enrdf_load_stackoverflow)
GR (1) GR3005608T3 (enrdf_load_stackoverflow)
IN (1) IN166787B (enrdf_load_stackoverflow)
PH (1) PH25093A (enrdf_load_stackoverflow)
ZA (1) ZA885491B (enrdf_load_stackoverflow)

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991015118A1 (en) * 1990-04-09 1991-10-17 Primavera Laboratories, Inc. Insect repellent lotions and sprays
US5227406A (en) * 1990-04-09 1993-07-13 Primavera Laboratories, Inc. Insect repellent lotions and sprays
US5254334A (en) * 1992-05-04 1993-10-19 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin amd emollients such as oils and esters
US5322685A (en) * 1989-08-03 1994-06-21 Hisamitsu Pharmaceutical Co., Inc. Skin cream preparation for external use
US5409706A (en) * 1992-05-04 1995-04-25 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin and emollients such as oils and esters
US5621013A (en) * 1992-06-24 1997-04-15 Primavera Laboratories, Inc. Insect replellent blends, lotions, and sprays
US5626839A (en) * 1994-11-08 1997-05-06 Scales-Medeiros; Virginia Light responsive self-tanning products and methods for use
US6139827A (en) * 1997-12-31 2000-10-31 L'oreal Wear cosmetic composition
US6299891B1 (en) 2000-03-14 2001-10-09 Amway Corporation Oil-free cosmetic composition
KR100374503B1 (ko) * 2000-11-28 2003-03-04 박계정 전기자 도선 권선기의 그립퍼 장치
US20030161851A1 (en) * 2002-02-14 2003-08-28 Bonne Bell, Inc. Cosmetic lip product with sour flavor
US6616923B1 (en) 2002-07-26 2003-09-09 Chiou Consulting, Inc. Aqueous compositions for facial cosmetics
US6649153B1 (en) 2002-09-16 2003-11-18 Reheis Inc. Skin friendly antiperspirant composition and method of making
US6652842B2 (en) 2001-11-13 2003-11-25 Noville, Inc. Deodorant compositions comprising diglycerol
US20040018220A1 (en) * 2002-07-26 2004-01-29 Chiou Consulting, Inc. Aqueous compositions for facial cosmetics
US6723304B2 (en) 2001-11-13 2004-04-20 Noville, Inc. Oral care compositions comprising diglycerol
US6723307B2 (en) 2002-02-14 2004-04-20 Bonne Bell, Inc. Cosmetic lip product with sour flavor
US6770264B2 (en) * 2001-11-13 2004-08-03 Noville, Inc. Chewing gum compositions comprising diglycerol
US20070077211A1 (en) * 2005-09-26 2007-04-05 Gc Corporation Composition for moistening oral cavity
US20110008445A1 (en) * 2006-10-23 2011-01-13 Mikiharu Okumura Suspension of ascorbic acid in glycerin and process for production thereof
WO2014134502A1 (en) * 2013-02-28 2014-09-04 Novan, Inc. Topical compositions and methods of using the same
US9289442B2 (en) 2011-07-05 2016-03-22 Novan, Inc. Topical compositions
US9427605B2 (en) 2005-03-24 2016-08-30 Novan, Inc. Cosmetic treatment with nitric oxide, device for performing said treatment and manufacturing method therefor
US9757397B2 (en) 2011-07-05 2017-09-12 Novan, Inc. Methods of manufacturing topical compositions and apparatus for the same
US20180042833A1 (en) * 2016-08-11 2018-02-15 XING YAN Plastic Co., Ltd. Cleaning Cream Containing PVA Particles and Producing Method Thereof
US10206947B2 (en) 2013-08-08 2019-02-19 Novan, Inc. Topical compositions and methods of using the same
US10226483B2 (en) 2013-08-08 2019-03-12 Novan, Inc. Topical compositions and methods of using the same
US20200155423A1 (en) * 2017-04-18 2020-05-21 Kao Corporation Method for producing coating
US10912743B2 (en) 2016-03-02 2021-02-09 Novan, Inc. Compositions for treating inflammation and methods of treating the same
CN112469386A (zh) * 2018-07-31 2021-03-09 花王株式会社 气溶胶化妆品
FR3104961A1 (fr) * 2019-12-20 2021-06-25 L'oreal Composition cosmetique comprenant au moins un polyol comportant au moins trois fonctions hydroxy et au moins un ester de sorbitan polyoxyethylene
US11166980B2 (en) 2016-04-13 2021-11-09 Novan, Inc. Compositions, systems, kits, and methods for treating an infection

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WO2006067645A1 (en) * 2004-12-20 2006-06-29 Firmenich Sa Personal care compositions comprising diglycerol
JP5635223B2 (ja) * 2006-07-07 2014-12-03 ポーラ化成工業株式会社 エステティック施術に好適な皮膚外用剤
JP5222465B2 (ja) * 2006-07-07 2013-06-26 ポーラ化成工業株式会社 エステティックに好適な皮膚外用剤
JP6207184B2 (ja) * 2013-03-14 2017-10-04 阪本薬品工業株式会社 化粧料及び皮膚外用剤

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Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5322685A (en) * 1989-08-03 1994-06-21 Hisamitsu Pharmaceutical Co., Inc. Skin cream preparation for external use
WO1991015118A1 (en) * 1990-04-09 1991-10-17 Primavera Laboratories, Inc. Insect repellent lotions and sprays
US5227406A (en) * 1990-04-09 1993-07-13 Primavera Laboratories, Inc. Insect repellent lotions and sprays
US5648398A (en) * 1990-04-09 1997-07-15 Primavera Laboratories, Inc. Insect repellent lotions and sprays
US5254334A (en) * 1992-05-04 1993-10-19 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin amd emollients such as oils and esters
US5409706A (en) * 1992-05-04 1995-04-25 Imaginative Research Associates, Inc. Anhydrous foaming composition containing low concentrations of detergents and high levels of glycerin and emollients such as oils and esters
US5621013A (en) * 1992-06-24 1997-04-15 Primavera Laboratories, Inc. Insect replellent blends, lotions, and sprays
US5626839A (en) * 1994-11-08 1997-05-06 Scales-Medeiros; Virginia Light responsive self-tanning products and methods for use
US6139827A (en) * 1997-12-31 2000-10-31 L'oreal Wear cosmetic composition
US6299891B1 (en) 2000-03-14 2001-10-09 Amway Corporation Oil-free cosmetic composition
KR100374503B1 (ko) * 2000-11-28 2003-03-04 박계정 전기자 도선 권선기의 그립퍼 장치
US6652842B2 (en) 2001-11-13 2003-11-25 Noville, Inc. Deodorant compositions comprising diglycerol
US6723304B2 (en) 2001-11-13 2004-04-20 Noville, Inc. Oral care compositions comprising diglycerol
US6770264B2 (en) * 2001-11-13 2004-08-03 Noville, Inc. Chewing gum compositions comprising diglycerol
US20030161851A1 (en) * 2002-02-14 2003-08-28 Bonne Bell, Inc. Cosmetic lip product with sour flavor
US6723307B2 (en) 2002-02-14 2004-04-20 Bonne Bell, Inc. Cosmetic lip product with sour flavor
US6616923B1 (en) 2002-07-26 2003-09-09 Chiou Consulting, Inc. Aqueous compositions for facial cosmetics
US20040018220A1 (en) * 2002-07-26 2004-01-29 Chiou Consulting, Inc. Aqueous compositions for facial cosmetics
US6649153B1 (en) 2002-09-16 2003-11-18 Reheis Inc. Skin friendly antiperspirant composition and method of making
US9427605B2 (en) 2005-03-24 2016-08-30 Novan, Inc. Cosmetic treatment with nitric oxide, device for performing said treatment and manufacturing method therefor
US20070077211A1 (en) * 2005-09-26 2007-04-05 Gc Corporation Composition for moistening oral cavity
US20110008445A1 (en) * 2006-10-23 2011-01-13 Mikiharu Okumura Suspension of ascorbic acid in glycerin and process for production thereof
US8211472B2 (en) * 2006-10-23 2012-07-03 Market Styles Co., Ltd. Suspension of ascorbic acid in glycerin and process for production thereof
US10265334B2 (en) 2011-07-05 2019-04-23 Novan, Inc. Anhydrous compositions
US10500220B2 (en) 2011-07-05 2019-12-10 Novan, Inc. Topical compositions
US9289442B2 (en) 2011-07-05 2016-03-22 Novan, Inc. Topical compositions
US9757397B2 (en) 2011-07-05 2017-09-12 Novan, Inc. Methods of manufacturing topical compositions and apparatus for the same
US9855211B2 (en) 2013-02-28 2018-01-02 Novan, Inc. Topical compositions and methods of using the same
US10258564B2 (en) 2013-02-28 2019-04-16 Novan, Inc. Topical compositions and methods of using the same
WO2014134502A1 (en) * 2013-02-28 2014-09-04 Novan, Inc. Topical compositions and methods of using the same
CN105392472A (zh) * 2013-02-28 2016-03-09 诺万公司 局部组合物及其使用方法
US11285098B2 (en) 2013-02-28 2022-03-29 Novan, Inc. Topical compositions and methods of using the same
CN105392472B (zh) * 2013-02-28 2021-08-10 诺万公司 局部组合物及其使用方法
US10206947B2 (en) 2013-08-08 2019-02-19 Novan, Inc. Topical compositions and methods of using the same
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US10828323B2 (en) 2013-08-08 2020-11-10 Novan, Inc. Topical compositions and methods of using the same
US11813284B2 (en) 2013-08-08 2023-11-14 Novan, Inc. Topical compositions and methods of using the same
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US11166980B2 (en) 2016-04-13 2021-11-09 Novan, Inc. Compositions, systems, kits, and methods for treating an infection
US20180042833A1 (en) * 2016-08-11 2018-02-15 XING YAN Plastic Co., Ltd. Cleaning Cream Containing PVA Particles and Producing Method Thereof
US20200155423A1 (en) * 2017-04-18 2020-05-21 Kao Corporation Method for producing coating
CN112469386A (zh) * 2018-07-31 2021-03-09 花王株式会社 气溶胶化妆品
FR3104961A1 (fr) * 2019-12-20 2021-06-25 L'oreal Composition cosmetique comprenant au moins un polyol comportant au moins trois fonctions hydroxy et au moins un ester de sorbitan polyoxyethylene

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BR8803709A (pt) 1989-02-14
DE3871640D1 (de) 1992-07-09
ZA885491B (en) 1990-03-28
DE3871640T2 (de) 1992-12-10
AU610911B2 (en) 1991-05-30
JPS6434910A (en) 1989-02-06
AU1974888A (en) 1989-01-27
ATE76744T1 (de) 1992-06-15
EP0301781A3 (en) 1989-06-14
GR3005608T3 (enrdf_load_stackoverflow) 1993-06-07
IN166787B (enrdf_load_stackoverflow) 1990-07-14
EP0301781B1 (en) 1992-06-03
EP0301781A2 (en) 1989-02-01
ES2033434T3 (es) 1993-03-16
PH25093A (en) 1991-02-19
CA1325599C (en) 1993-12-28
JPH07106967B2 (ja) 1995-11-15

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